Enantioselective Synthesis of α-Alkylidene-γ-Butyrolactones: Intramolecular Rauhut–Currier Reaction Promoted by Acid/Base Organocatalysts


  • This work was supported by the CREST project of the Japan Science and Technology Corporation (JST) and a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). We thank the Deutsche Forschungsgemeinschaft (scholarship for A.G., International Research Training Group “Selectivity in Chemo- and Biocatalysis”—SeleCa (Germany)). We acknowledge the technical staff of the Comprehensive Analysis Center of ISIR, Osaka University (Japan).


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Teaming up: The title reaction has been developed to deliver the product α-alkylidene-γ-butyrolactones as single diastereomers with up to 98 % ee (see scheme; Ts=4-toluenesulfonyl). The enantioselective process is catalyzed by 1, which contains both Lewis base and Brønsted acid moieties.